Spellbook

LegalTech

PrincipalSecurityResearcher

CA$202–252k Canada FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Senior candidates.

The Brief

“Principal Security Researcher at Spellbook. Skills: Security Research, Offensive Security, AI Security, LLM Security, Product Security, Red Teaming, Threat Modeling. Identify security risks across the company and partner with the relevant teams to reduce them. Lead active red teaming, application security testing, penetration testing, exploit validation, and adversarial analysis”

What You'll Achieve.

protect that trust at the source; reduce risk across Spellbook's products, infrastructure, AI workflows, and internal operations; raises the maturity of how Spellbook approaches red teaming, threat modelling, bug bounty triage, and incident response; reduce security risks; driving measurable risk reduction

Industry & Context.

LegalTech
Problems you'll solve

identify security risks; validate real-world impact; reduce risk; distinguishing theoretical risk from practical risk; focus on what matters most

What They're Looking For.

Must Have

experience in application security, red teaming, penetration testing, vulnerability research, product security, or offensive security, Hands-on experience testing modern web applications, APIs, authentication flows, authorization models, cloud services, and distributed systems, Experience developing proof-of-concept exploits or clear technical demonstrations to validate security impact, Firm grasp of common software security risks, secure design principles, identity and access controls, data protection, and secure development practices, Experience partnering with engineering, product, or R&D teams to triage, prioritize, and remediate vulnerabilities end-to-end, Excellent written and verbal communication skills, with the ability to write clear technical reports, executive summaries, remediation guidance, and public-facing research, and to explain trade-offs to engineers, PMs, and leadership, judgment around responsible disclosure, customer impact, confidentiality, and coordinated communication, Pragmatic at distinguishing theoretical risk from practical risk, with the instinct to help teams focus on what matters most, Comfortable operating with ambiguity and moving with urgency across hands-on testing, product security, incident support, and external coordination, Track record of driving measurable risk reduction in a fast-moving technical environment

Nice to Have

Experience with AI security, LLM security, prompt injection, jailbreaks, agentic workflows, model abuse, or secure AI product development, Experience in legaltech, fintech, healthtech, or another environment that handles highly sensitive customer data, Experience managing or participating in bug bounty programs, responsible disclosure programs, or external researcher communities, Experience publishing security research, speaking at conferences, or contributing to the broader security research community, Familiarity with enterprise security expectations and compliance frameworks such as SOC 2, HIPAA, GDPR, or emerging AI governance frameworks

What You'll Do.

Identify security risks across the company and partner with the relevant teams to reduce them

Lead active red teaming

application security testing

and adversarial analysis

Conduct original security research on legal AI

sensitive document workflows

Coordinate third-party penetration tests

and other external security assessments

Own external vulnerability reports — bug bounty submissions

responsible disclosure reports

researcher communications

and remediation tracking

Drive threat modelling and secure design reviews for new products

and infrastructure changes

Partner with R&D and Engineering to surface trust boundaries

and data exposure risks early in development

Support Security Operations during incident response by reproducing vulnerabilities

and recommending remediation

Engage with frontier AI labs

and the broader security community to stay current on AI safety and security developments

Publish security research

or conference talks where aligned with company priorities

Define and improve repeatable processes for security research

vulnerability management

and remediation across Spellbook

Support with other responsibilities and projects as required

How You'll Work.

Team & Collaboration

partner with the Director of Security & IT; work across the company; secure product development partnerships with R&D and Engineering; Partner with R&D and Engineering to surface trust boundaries, abuse cases, and data exposure risks early in development; Support Security Operations during incident response; Engage with frontier AI labs, external researchers, vendors, and the broader security community

Communication Scope

Excellent written and verbal communication skills; ability to write clear technical reports, executive summaries, remediation guidance, and public-facing research; explain trade-offs to engineers, PMs, and leadership; coordinated communication

Process & Methodology

program-level work that raises the maturity of how Spellbook approaches red teaming, threat modelling, bug bounty triage, and incident response, Define and improve repeatable processes for security research, testing, vulnerability management, and remediation across Spellbook

Full Job Description

Spellbook is the most comprehensive AI copilot for transactional lawyers. It works directly inside Microsoft Word to help legal teams draft, review, and negotiate contracts up to 10x faster and with greater precision. Today, more than 4,000 law firms, in-house teams, and solo practitioners rely on Spellbook to simplify their workflows and eliminate the drudgery of everyday contract work. We are backed by leading investors including Khosla Ventures, Thomson Reuters Ventures, Inovia Capital, The LegalTech Fund, Bling Capital, and Moxxie Ventures. The company recently raised $50 million in Series B funding, led by Keith Rabois at Khosla Ventures, bringing its total funding to more than $80 million. *This is an existing vacancy ABOUT THE ROLE Legal teams worldwide trust Spellbook with their most sensitive data, and we're looking for a Principal Security Researcher to help us protect that trust at the source. You'll partner with the Director of Security & IT and work across the company to identify security risks, validate real-world impact, and reduce risk across Spellbook's products, infrastructure, AI workflows, and internal operations. This is a senior individual contributor role with broad influence. You'll move between original security research on legal AI and LLM-enabled workflows, hands-on offensive testing, secure product development partnerships with R&D and Engineering, and program-level work that raises the maturity of how Spellbook approaches red teaming, threat modelling, bug bounty triage, and incident response. RESPONSIBILITIES • Identify security risks across the company and partner with the relevant teams to reduce them. • Lead active red teaming, application security testing, penetration testing, exploit validation, and adversarial analysis. • Conduct original security research on legal AI, LLM-enabled products, sensitive document workflows, prompt injection, data leakage, model misuse, and tool abuse. • Coordinate third-party penetration tests, red te

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